East Winter Garden
Winter Garden’s story isn’t only the story of Plant Street.
During the early decades of the twentieth century, East Winter Garden developed as the city’s African-American community.
According to the City of Winter Garden’s history of the community, Black residents purchased land around what became the Center Street area, which was then largely lowland.
Center Street began as little more than a rough dirt road connecting with Plant Street.
Eventually, it became the heart of a community.
Some residents came because of work available in the surrounding pine forests, harvesting pine gum and producing turpentine.
Others found employment in citrus groves and packinghouses.
In 1910, J.S. Loveless platted the Loveless Addition near Plant Street.
Churches became important centers of community life. Schools initially operated within churches before the Winter Garden Colored School opened on Center Street in 1923.
Businesses developed too.
One particularly long-lived piece of that history is Dyson’s Plaza.
George and Annie Bell Dyson purchased the property in 1939. Over generations, the site housed businesses including a beer garden and juke joint, taxi service, ice house, convenience store and other neighborhood businesses.
East Winter Garden also produced residents who changed the city itself.
Juanita Coney Maxey became the first African-American woman known to vote in Winter Garden in the 1930s.
Charles Alexander King became Winter Garden’s first Black police officer in 1967.
And in 1985, Mildred Dixon became both the first woman and first African-American elected to the Winter Garden City Commission.
Those stories are part of Winter Garden too.
The city’s history makes considerably less sense if we tell only the part visible from a restaurant table on Plant Street.
Both communities helped build Winter Garden.
And both were about to experience enormous change.
